Luxury 5-Day Italy City Break in Siena

Your exciting luxury holiday begins as soon as you arrive in the beautiful city of Siena. You will stay in the city for 4 nights and choose from some of the best luxury hotels in downtown Siena that are guaranteed to make you feel special.

Tonight, you will be treated to a stay at one of the best luxury hotels in Siena. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

Begin your sightseeing with a visit to Porta Camollia. This city gate is rated an average of 4.5 out of 5 stars in 2,460 reviews.

Exploring new places can make you hungry. When you’re ready for dinner, we recommend trying one of the finest restaurants in Siena.

Locals enjoy eating at Osteria La Sosta di Violante, one of the most recommended restaurants in Siena. This city restaurant has an average rating of 4.7 out of 5 stars from 2,042 customers.

Many patrons praise its unique ambiance and attentive service, making it a must-visit for both locals and tourists alike.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

When an after-dinner drink sounds enticing, visit La Taverna di San Giuseppe, one of the best bars in the city of Siena. This bar has an average rating of 4.7 out of 5 stars from 1,767 customers.

Celebrate the start of your 5-day city break in Siena with a toast!

As the sun rises on day 2 in Siena, greet the day with excitement. Today offers the perfect opportunity to delve deeper into the city's rich history and vibrant culture. Whether you're embarking on guided tours, discovering famous attractions, or simply relaxing in the city's scenic beauty, every moment is an invitation to indulge in luxury and discovery.

Start your day with a visit to Duomo di Siena. This extraordinary domus is rated an average of 4.8 out of 5 stars by 21,656 visitors.

Next, make your way to Pubblico Palace. This top attraction is a museum with an average rating of 4.7 out of 5 stars by 1,400 visitors.

We also recommend a visit to Piazza del Campo. This square is rated 4.8 out of 5 stars by 64,175 travelers.

If you’re keen to keep exploring, visit Tower of Mangia. This highly recommended sightseeing destination has received an average rating of 4.6 out of 5 stars from 673 travelers.

Today is also your chance to spend some time at Loggia del Papa, Siena. This sightseeing destination is rated an average of 4.5 out of 5 stars by 235 travelers.

To do something one-of-a-kind on this day of your trip, you can join a tour. You can discover all of the most fun and eye-opening experiences in your destination below and secure your spot here.

After a long day of discovering the unique sights of Italy, it’s an excellent idea to sit down for a lovely meal. We’ve collected the most recommended restaurants in the city of Siena for you, so you can check out their menus and make your reservation in advance.

Reserve your spot at Osteria degli Svitati, a popular local restaurant in Siena. This culinary hotspot and its flavorful dishes have left a lasting impression on guests. Its dedication to culinary mastery is reflected by its 4.7 out of 5-star rating from 911 satisfied guests.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

Celebrate this wonderful day with sumptuous cocktails at Ristorante Gallo Nero, a terrific bar to unwind after a busy day. Around 829 customers rated this bar with an impressive average of 4.4 out of 5 stars.

Raise a toast to another amazing day of your luxury holiday in Siena! Get some rest at your hotel in preparation for yet another fantastic day in Italy.

On day 3 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Siena. You’ll stay in Siena for 2 nights, which gives you enough time to discover some of the most amazing things to see and do in the city.

Seize the day by visiting some of the best attractions in the area, like Palazzo Salimbeni. This extraordinary palazzo has an average rating of 4.5 out of 5 stars from 2,537 visitors.

Next, make your way to Santuario Casa di Santa Caterina. This shrine is rated an average of 4.6 out of 5 stars in 1,201 reviews.

While in Siena, we also recommend a visit to Basilica Cateriniana San Domenico. This minor basilica has been rated an average of 4.6 out of 5 stars in 3,290 reviews.

If you’re keen to explore even more, then consider a visit to Vista Panoramica de Siena. With an average rating of 4.8 out of 5 stars by 194 travelers, this point of interest is a highly recommended stop on your sightseeing around Siena.

Make your way to Fortezza Medicea, perhaps the most famous fortress in Siena. This attraction is rated an average of 4.5 out of 5 stars in 9,835 reviews.

One of the most unique ways of discovering what else Siena has to offer is by going on a top-rated tour. Be sure to check out all the experiences Siena offers and add your favorites to your Italy travel package below.

After a long day of exploring, it’s time for indulging in some food. Make a reservation at one of the best restaurants in Siena.

Elevate your experience by savoring a meal in Osteria Il Carroccio, a distinguished dining establishment in Siena. It has a rating of 4.7 out of 5 stars, thanks to the positive reviews of 895 satisfied guests and a menu that’s committed to quality and flavor.

As your first day in Siena is coming to an end, retreat to a bar for some celebration. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

To have one of the best bar experiences in Siena, we recommend going to the wonderful San Paolo Pub. This bar offers a variety of phenomenal dishes and drinks and has been rated an average of 4.3 out of 5 stars by 704 customers.

This is a favorite place to hang out among locals, and an excellent place to visit if you wish to make new acquaintances while enjoying a refreshing drink.

No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed. Cheers to a fantastic day of your luxury vacation in Siena, Italy!

Wake up refreshed to day 4 of your luxury holiday in Siena. Today, you're going to experience the perfect blend of discovery, excitement, and indulgence. Take the opportunity to see the best sights, join the most exciting activities, and sample the finest restaurants in the city. Cherish the 1 night you have left of your luxury holiday in Siena.

When you’re ready for some sightseeing, make your way to Porta Tufi. This much-appreciated city gate is rated 4.5 out of 5 stars in 906 reviews.

Next up is Musei dell’Accademia dei Fisiocritici. This museum has an average rating of 4.8 out of 5 stars from 280 visitors.

Another top sightseeing recommendation is Pinacoteca Nazionale di Siena. This art museum has been rated 4.3 out of 5 stars in 507 reviews. Every year, 8,127 travelers include this attraction on their travel itinerary.

Porta Romana is another attraction you have the opportunity to visit today. This city gate has an average rating of 4.4 out of 5 stars from 2,383 reviews.

Your discoveries in Siena do not have to stop there. Check out the fantastic selection of tours and tickets offered in Siena on this day of your trip. You can select your tours below.

After a long day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Book a table at Antica Trattoria Papei, a famous dining establishment in Siena. This culinary hotspot and its delectable cuisine have captured the hearts of food enthusiasts. Its reputation for food excellence is reflected in its 4.3 out of 5-star rating from 3,761 satisfied diners.

Go back to your hotel, take a stroll through the city, or head out to a bar to celebrate another fantastic day of your luxury vacation in Siena.

If you’re up for classic drinks with a modern flair, consider going to Bar Impero Siena. Around 988 customers have given this incredible bar an average rating of 4.2 out of 5 stars.

Go over your photos from the day, raise a toast, and rest your tired legs. Another wonderful day of your luxury holiday in Siena awaits!

Your luxurious city break in Siena is coming to an end, and it's soon time to say goodbye to the city. But before you leave, make sure to capture a few more memories and perhaps find that special souvenir to remind you of your unforgettable journey.

As your final day in Italy unfolds, don’t miss the chance for a last-minute shopping spree in Siena’s shopping district. Your accommodation’s convenient location near the city’s shopping area offers the luxury of time, so you don’t have to limit yourself from leisurely strolling its streets amidst a collection of establishments.

Look for the perfect gift for your loved ones back home, or buy yourself a little keepsake to remind you of Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Porta Pispini. This extraordinary sightseeing destination and attraction is rated an average of 4.5 out of 5 stars in 1,437 reviews, and is an excellent choice for your last sightseeing in Siena.

Don’t travel hungry. Take the opportunity to savor the local cuisine in Siena one last time before you head to the airport.

This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.6 out of 5 stars from 1,669 reviews.

You will then say farewell to Siena and begin your journey home. Now with a camera roll full of photos and your memory filled with happy moments from your unforgettable luxury holiday in Siena, Italy!